How many flights depart from Wisconsin to Caribbean Islands on average per week?

As of September 2025, 25 flights take off from Wisconsin and land in Caribbean Islands each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

What airlines fly to Caribbean Islands?

American Airlines, Delta and United Airlines are the top three most popular airlines that fly to Caribbean Islands from Wisconsin according to our data. American Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 7 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Wisconsin to Caribbean Islands?

Arajet, Spirit Airlines, and United Airlines are the most popular carriers operating from Wisconsin to Caribbean Islands

How long is the flight from Wisconsin to Caribbean Islands?

The flight from Wisconsin to Caribbean Islands depends on which airports you’re departing and arriving from and whether or not you have a layover. If you fly from Madison (a popular airport in Wisconsin) to Copenhagen (the most popular airport in Caribbean Islands), then the flight time is 12h 12m on average. If you fly from Milwaukee (another popular airport in Wisconsin) to Copenhagen, then the average flight time is 15h 36m.

When did momondo last update prices for flights from Wisconsin to Caribbean Islands?

Prices for flights from Wisconsin to Caribbean Islands refresh daily.

How many operators does momondo search for flights from Wisconsin to Caribbean Islands?

As of September 2025, there are 12 operators available to choose from for flights from Wisconsin to Caribbean Islands.

How old do you have to be to fly from Wisconsin to Caribbean Islands?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$93 Cheap Flights from Wisconsin to Caribbean Islands in 2025/26

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Find the cheapest flights from Wisconsin to Caribbean Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

11:55 am - 2:59 pmORD-SJU

26h 04m2 stops

9:48 am - 1:56 pmSJU-ORD

5h 08mnonstop

$207Spirit Airlines

Find Deal

Sat, Oct 11 - Sat, Oct 18

9:06 pm - 2:51 amORD-SJU

4h 45mnonstop

3:19 pm - 9:33 pmSJU-ORD

7h 14m1 stop

$208Spirit Airlines

Find Deal

Fri, Oct 24 - Wed, Oct 29

2:20 pm - 8:00 pmORD-SJU

4h 40mnonstop

8:10 am - 11:32 amSJU-ORD

5h 22mnonstop

$218United Airlines

Find Deal

Tue, Oct 28 - Mon, Nov 3

6:40 am - 2:02 amORD-SJU

18h 22m1 stop

7:43 pm - 11:57 pmSJU-ORD

5h 14mnonstop

$219Multiple Airlines

Find Deal

Wed, Oct 22 - Fri, Oct 31

9:06 pm - 2:51 amORD-SJU

4h 45mnonstop

9:00 am - 12:45 pmSJU-ORD

28h 45m1 stop

$220Multiple Airlines

Find Deal

Fri, Oct 24 - Tue, Oct 28

6:40 am - 3:24 pmORD-SJU

7h 44m1 stop

11:48 am - 1:31 amSJU-ORD

14h 43m2 stops

$222Frontier

Find Deal

Wed, Oct 15 - Fri, Oct 24

9:45 am - 11:59 pmORD-SJU

13h 14m1 stop

3:00 pm - 7:20 pmSJU-ORD

5h 20mnonstop

$223American Airlines

Find Deal

Wed, Oct 15 - Wed, Oct 22

8:35 am - 10:10 pmORD-SJU

12h 35m1 stop

3:43 pm - 7:21 pmSJU-ORD

5h 38mnonstop

$224American Airlines

Find Deal

Thu, Oct 30 - Thu, Nov 6

6:40 am - 3:24 pmORD-SJU

7h 44m1 stop

12:11 pm - 11:39 pmSJU-ORD

12h 28m2 stops

$225Frontier

Find Deal

Wed, Oct 15 - Thu, Oct 23

11:30 am - 9:00 pmMKE-SJU

7h 30m1 stop

2:05 am - 12:09 pmSJU-MKE

12h 04m2 stops

$323United Airlines

Find Deal

Sun, Feb 1 - Fri, Feb 6

Frontier flights from Wisconsin to Caribbean Islands

Our best Frontier deals on Wisconsin to Caribbean Islands flight tickets

Frontier

Oct 15

ORD6:40 amChicago O'Hare Intl

7h 44m

1 stop

SJU3:24 pmSan Juan Luis Munoz Marin Intl

Oct 24

SJU11:48 amSan Juan Luis Munoz Marin Intl

14h 43m

2 stops

ORD1:31 amChicago O'Hare Intl

$222

Find similar

Frontier

Oct 15

ORD6:40 amChicago O'Hare Intl

7h 44m

1 stop

SJU3:24 pmSan Juan Luis Munoz Marin Intl

Oct 23

SJU12:11 pmSan Juan Luis Munoz Marin Intl

12h 28m

2 stops

ORD11:39 pmChicago O'Hare Intl

$225

Find similar

Frontier

Oct 28

ORD6:40 amChicago O'Hare Intl

10h 14m

1 stop

SJU5:54 pmSan Juan Luis Munoz Marin Intl

Nov 3

SJU9:00 amSan Juan Luis Munoz Marin Intl

29h 45m

1 stop

ORD12:45 pmChicago O'Hare Intl

$226

Find similar

Spirit Airlines flights from Wisconsin to Caribbean Islands

Our best Spirit Airlines deals on Wisconsin to Caribbean Islands flight tickets

Spirit Airlines

Oct 11

ORD11:55 amChicago O'Hare Intl

26h 04m

2 stops

SJU2:59 pmSan Juan Luis Munoz Marin Intl

Oct 18

SJU9:48 amSan Juan Luis Munoz Marin Intl

5h 08m

ORD1:56 pmChicago O'Hare Intl

$207

Find similar

Spirit Airlines

Oct 24

ORD9:06 pmChicago O'Hare Intl

4h 45m

SJU2:51 amSan Juan Luis Munoz Marin Intl

Oct 29

SJU3:19 pmSan Juan Luis Munoz Marin Intl

7h 14m

1 stop

ORD9:33 pmChicago O'Hare Intl

$208

Find similar

Spirit Airlines

Sep 22

ORD6:30 amChicago O'Hare Intl

6h 41m

1 stop

SJU2:11 pmSan Juan Luis Munoz Marin Intl

Oct 2

SJU11:59 amSan Juan Luis Munoz Marin Intl

6h 40m

1 stop

ORD5:39 pmChicago O'Hare Intl

$210

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Wisconsin to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 10/11

11:55 am-2:59 pm

2 stops26h 04m

San Juan Luis Munoz Marin Intl

Sat 10/18

9:48 am-1:56 pm

Nonstop5h 08m

$207

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/24

9:06 pm-2:51 am

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Wed 10/29

3:19 pm-9:33 pm

1 stop7h 14m

$208

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/28

2:20 pm-8:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Mon 11/3

8:10 am-11:32 am

Nonstop5h 22m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/22

6:40 am-2:02 am

1 stop18h 22m

San Juan Luis Munoz Marin Intl

Fri 10/31

7:43 pm-11:57 pm

Nonstop5h 14m

$219

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/24

9:06 pm-2:51 am

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Tue 10/28

9:00 am-12:45 pm

1 stop28h 45m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/15

6:40 am-3:24 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Fri 10/24

11:48 am-1:31 am

2 stops14h 43m

$222

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/15

9:45 am-11:59 pm

1 stop13h 14m

San Juan Luis Munoz Marin Intl

Wed 10/22

3:00 pm-7:20 pm

Nonstop5h 20m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 10/30

8:35 am-10:10 pm

1 stop12h 35m

San Juan Luis Munoz Marin Intl

Thu 11/6

3:43 pm-7:21 pm

Nonstop5h 38m

$224

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/15

6:40 am-3:24 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Thu 10/23

12:11 pm-11:39 pm

2 stops12h 28m

$225

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 2/1

11:30 am-9:00 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-12:09 pm

2 stops12h 04m

$323

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How to get the cheapest flight ticket from Wisconsin to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Wisconsin, with most prices found around $317. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Wisconsin averaging around $347.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Wisconsin to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $389. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $477. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Wisconsin to Caribbean Islands in the evening for as low as $360. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $458. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Wisconsin to Caribbean Islands flight route?

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl for the best Wisconsin - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $433 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Wisconsin for as low as $351 on momondo.

What cabin class options are available on Wisconsin to Caribbean Islands flights?

There is only 1 cabin class available to choose from on Wisconsin to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Caribbean Islands.

Cheap Wisconsin to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Caribbean Islands

Fastest flight time	3h 18m
Direct flights	Every day
Airports in Caribbean Islands	3 airports

The fastest flight from Wisconsin to Caribbean Islands takes 3h 18m

Direct flights go from Wisconsin to Caribbean Islands every day.

There are 3 airports near Caribbean Islands: Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ), Providenciales (PLS)

Search flight deals

When did momondo last update prices for flights from Wisconsin to Caribbean Islands?
Prices for flights from Wisconsin to Caribbean Islands refresh daily.
How many operators does momondo search for flights from Wisconsin to Caribbean Islands?
As of September 2025, there are 12 operators available to choose from for flights from Wisconsin to Caribbean Islands.
How old do you have to be to fly from Wisconsin to Caribbean Islands?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Wisconsin to Caribbean Islands?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Wisconsin to Caribbean Islands is Airbus A320-100/200 (22.22% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (8.87%), Boeing 737 MAX 8 (8.39%), and Boeing 737-800 Passenger/BBJ2 (winglets) (7.48%).

Best airlines flying from Wisconsin to Caribbean Islands

Compare and see reviews for airlines that fly from Wisconsin to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $129	Free Cancellation	Rating 5.8 3,174 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $208	Free Cancellation	Rating 6.3 8,019 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $215	Free Cancellation	Rating 7.4 8,924 reviews	Search United Airlines flights
Delta	PriceFrom $215	Free Cancellation	Rating 7.9 7,957 reviews	Search Delta flights
American Airlines	PriceFrom $274	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
Sun Country Air	PriceFrom $540	Free Cancellation	Rating 6.9 330 reviews	Search Sun Country Air flights

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Wisconsin to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Wisconsin to Caribbean Islands with flexible booking policies on momondo?

Yes. All flights to Caribbean Islands from Wisconsin on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Wisconsin to Caribbean Islands?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Wisconsin. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Wisconsin to Caribbean Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Wisconsin to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Popular cities in Caribbean Islands

Flights to New Yorkfrom $49

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Flights to Tokyofrom $374

Flights to Los Angelesfrom $49

Flights to Parisfrom $360

Flights to Copenhagenfrom $369

Flights to Istanbulfrom $397

Flights to Manilafrom $523

Flights to Romefrom $340

Flights to Miamifrom $49

Flights to Chicagofrom $49

Cheap flights from Wisconsin to Caribbean Islands from $93

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Caribbean Islands departing on 11/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Wisconsin to Caribbean Islands

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Wisconsin to Caribbean Islands

Our best Frontier deals on Wisconsin to Caribbean Islands flight tickets

Spirit Airlines flights from Wisconsin to Caribbean Islands

Our best Spirit Airlines deals on Wisconsin to Caribbean Islands flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Wisconsin to Caribbean Islands that are best for you.

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Wisconsin to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Wisconsin, with most prices found around $317. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Wisconsin averaging around $347.

What is the cheapest day to depart on your flight to Caribbean Islands?

What is the cheapest time of day to depart on your flight to Caribbean Islands?

What is the cheapest Wisconsin to Caribbean Islands flight route?

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl for the best Wisconsin - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

What cabin class options are available on Wisconsin to Caribbean Islands flights?

There is only 1 cabin class available to choose from on Wisconsin to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Caribbean Islands.

What is the cheapest airline that flies from Wisconsin to Caribbean Islands?

Arajet, Spirit Airlines, and United Airlines are the most popular carriers operating from Wisconsin to Caribbean Islands

What airlines fly to Caribbean Islands?

How many flights depart from Wisconsin to Caribbean Islands on average per week?

As of September 2025, 25 flights take off from Wisconsin and land in Caribbean Islands each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

How long is the flight from Wisconsin to Caribbean Islands?

Cheap Wisconsin to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Caribbean Islands

Fastest flight time

Direct flights

Airports in Caribbean Islands

When did momondo last update prices for flights from Wisconsin to Caribbean Islands?

How many operators does momondo search for flights from Wisconsin to Caribbean Islands?

How old do you have to be to fly from Wisconsin to Caribbean Islands?

What documentation or ID do you need to fly to Caribbean Islands?

What is the most popular plane model from Wisconsin to Caribbean Islands?

Best airlines flying from Wisconsin to Caribbean Islands

Compare and see reviews for airlines that fly from Wisconsin to Caribbean Islands with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Caribbean Islands?

Can I find flights from Wisconsin to Caribbean Islands with flexible booking policies on momondo?

How can momondo help me find flights from Wisconsin to Caribbean Islands?

I’m not ready to book a flight from Wisconsin to Caribbean Islands right now. Can momondo alert me if prices change?

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo